


Every Damn Day

by Spunkybob5



Series: A Night of Free Will [3]
Category: Supernatural
Genre: Coffee, Explicit Sexual Content, F/M, Fluff, Fluff and Smut, Light Angst, Pie, Porn With Plot, Sex, Smut
Language: English
Status: Completed
Published: 2016-06-30
Updated: 2016-06-30
Packaged: 2018-07-19 03:32:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,065
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7343086
Author URL: https://archiveofourown.org/users/Spunkybob5/pseuds/Spunkybob5
Summary: <blockquote class="userstuff">
              <p>Your first time with Dean.</p>
            </blockquote>





	Every Damn Day

**Author's Note:**

> So far this series has taken place outside of time. My intention was to do that with Dean's story as well, but I think some clarity is in order. This is not first season Dean. Sleeping with the Dean from the pilot would be nothing like sleeping with Dean from the end of Season 11. This story features modern Dean.

I did not open The Coffee Shop to meet hot guys.

It just happens to be one of the “perks.” (See what I did there? Ha ha! I crack me up.)

Anyway.

The Coffee Shop isn’t like a Starbucks. I mean, I have espresso, but in bean form. I carry gourmet coffees from all over the world – Turkey, Kenya, Colombia, everywhere. Mostly I cater to hipsters, but occasionally I encounter clients who are getting a little older and just want some of the finer things in life.

Dean was one of those.

He first walked in on a Thursday. “Can I help you?” I asked sweetly, trying not to ogle him.

“Hi, yeah,” he scratched the back of his neck. “I’m looking for coffee.”

“Well, you’re in luck. I sell a little of that here.”

He grinned, “I thought the name on the door was a good clue.”

“You’re obviously very clever,” I nodded seriously. “Are you looking for anything in particular?”

“Um, I’m not really sure. I’ve spent most of my life drinking whatever sludge I could get at the gas station, but lately I’ve had more time to…savor,” he cleared his throat. “I thought maybe I could treat myself.”

“There’s nothing wrong with wanting the finer things in life, um…?”

“Dean,” he offered his hand.

“Nice to meet you, Dean,” I introduced myself as owner. “So tell me, how do you take your coffee?”

“Black. Sometimes with a little sugar.”

“And do you like a little bite, a little bitterness?”

“Nah, I like it smooth,” he winked.

I may have blushed. And giggled. I took his flirtatiousness as an opportunity to appraise him. Dean was gorgeous. Broad shoulders, powerful arms, strong chest, narrow waist, long fingers. I’m into all of that. But what really set Dean apart was his face. He’s so pretty. Bright green eyes, high cheekbones, marble jaw, and lips…God, his lips. Perfect. Just…so kissable. And suckable. And lickable. And…what was I saying?

I snapped back to reality, chastising myself. _Don’t creep out the customers._ Dean didn’t seem to mind, though. I think he was looking at me the same way I was examining him.

“Ok, so not bitter,” I said, attempting to be professional. “I have some samples over here you might like.”

That first night, Dean spent about thirty minutes in The Coffee Shop, listening to me blabber about the nuances of coffee. When he left, it was with three small bags of coffee, a French press, a coffee grinder, and a promise to be back.

Dean kept his promise, reappearing in the store the following Tuesday. “Hey,” he greeted, a warm smile on his perfect lips.

“Hey, yourself. Need more coffee already?”

He scrubbed his hand across the back of his neck, “Yeah. My brother got all excited…we went through all of it this weekend.”

My eyes widened, “ALL of it? Did you even sleep?”

Dean grinned, “Not as much as I should have.”

I laughed, “So do you want more of the same, or do you want to try different selections?”

“Some of both, actually,” Dean reached into his back pocket and produced a crumpled piece of paper. “I did some research. You know, when I couldn’t sleep.”

“You did? I’m so impressed!”

“What can I say?” Dean shrugged, flashing another panty-melting smile. “You inspired me.”

***

For the next couple months, Dean dropped by at least weekly, often more. We flirted and smiled and it was charming, but I really didn’t think it was going anywhere. I mean, I have enough class to not ask out my customers, and anyway, how could a guy that smart and sweet and ridiculously sexy be single?

Still, I found myself distracted by thoughts of those green eyes and perfect lips. So much so that when I was cleaning up after work on Friday, it took me a while to notice the knock at my door.

“Dean!” I unlocked the door, opening it wide to let him in.

“Hey,” he smiled shyly.

“What are you doing here? You need coffee that badly at eight o’clock on a Friday night?”

“No, actually. I just had a really long week, and I wondered if you’d like to get some pie with me.”

I tilted my head, “Like – a date?”

“Yeah,” Dean licked his lips and shifted his weight. “Like a date.”

My smile damn near split my face in two, “I would love that.”

Twenty minutes later found me sitting across from Dean in a little café that, apparently, had the best pie in town. Dean ordered three different flavors for us to try – turns out you can never have too much pie – and we talked about nothing important at all. Dean had some strongly held opinions on the Marvel Cinematic Universe, and we debated whether Stucky or Stoney had more merit.

Two hours and an obscene amount of pie later, Dean and I stood to leave. “Can I walk you back to your car?” he offered.

“No, but you can walk me home.”

“Oh. You live close?”

“You could say that,” I answered, taking the lead.

Dean fell in step next to me, taking my hand gently.

I let him.

We walked in companionable silence until we reached The Coffee Shop.

“You live here?” Dean asked.

“Yeah. Well, above it. There’s a little apartment up there.”

Dean grinned, “Your house must smell amazing!”

I laughed, “Yes, I suppose it does.” I turned to thank Dean for a nice evening, but at his expression, the words died on my tongue.

Dean leaned in, pressing a soft kiss to my lips. He smelled of coffee and motor oil and that old school masculine aftershave. His mouth was every bit as perfect as it looked, and he tasted like pie. I sighed into the kiss.

Dean pulled away (far too soon) and smiled shyly, “I had a really nice time. Do you think we could do it again sometime?”

I squeezed his hand, “I’d like that.”

“Great!” Dean’s smile turned vibrant. “Listen, can you do one little favor for me?”

“What’s that?”

“Will you wave to me when you get into your apartment? I just want to make sure you’re safely inside.”

“Of course.”

***

The next Friday, pie turned into dinner. The week after that, dinner and drinks. After that, dinner, drinks, and a movie. For six weeks, we progressed that way. We talked about everything – except Dean’s job. He never brought it up, and I didn’t ask. I could tell he didn’t want to share, and that was fine.

I was far more preoccupied trying to figure out why we weren’t having sex.

As the length of our dates increased, so did the intensity of our good night kiss. By date five, Dean had me pressed against the brick of the building, writhing against him while his tongue plundered my mouth. But when I asked him to come upstairs, the answer was always the same:

“Not yet, baby.”

The night of our seventh date ended a little differently, though.

Dean had been quiet all night, hardly commenting on the movie and barely touching his pie.

“Hey,” I said, bumping him as we walked back to The Coffee Shop. “What’s up?”

“Nothing.”

I raised my eyebrows and stared at him.

Dean sighed, running his hand over his face, “Ok, not nothing. I’m leaving town tomorrow.”

“Oh,” I said. “Forever?”

“No! At least, I hope not,” Dean sighed again. “But I don’t know how long I’ll be gone.”

“Are we talking days? Months? Years?” I could feel my stomach clench.

“Not years,” Dean shook his head. “Probably more like weeks. But – my job, it’s…” He trailed off, not meeting my eyes.

“It’s dangerous,” I finished.

“Yes.”

“Is it important?”

Dean met my gaze, “Very.”

“Then I don’t need to know,” I said. “But, Dean?”

“Yeah?”

“Please be safe. I’d miss you.”

Dean’s eyes widened just a little, and he squeezed my hand.

We walked in silence. And when he kissed me good night, it felt a lot like being kissed goodbye.

***

For the first two weeks, I worried about Dean constantly. A mild nausea plagued most of my waking hours, and my nights were peppered with stress dreams. I berated myself for not having his phone number or even his address. I chastised myself for not asking about any mutual friends we might have.

Who would know to tell me if he died?

It turns out my body can’t sustain that level of stress. Over time, I went from worrying constantly, to worrying sometimes, to wondering what had happened to Dean.

By the time two months had passed, I resigned myself to the idea that I’d probably never know. And it hurt, but it was probably better for my mental health than either thinking he’d died or waiting on pins and needles for him to reappear.

Six months to the day from the first time Dean appeared in The Coffee Shop found me helping a whiny older woman pick out just the right coffee blend for her visiting son. She’d started on chapter 17 of her life story, and I was no longer listening. I filled a bag with the beans she’d requested, nodding absently to her drivel, when the bell rang above the door.

“Be right with you,” I called without turning.

“Take your time.”

My heart stopped. I thrust the bag at the woman, “Get out.”

“But – I haven’t paid,” she stuttered.

I literally shoved her towards the door, “On the house. Enjoy your son’s visit.” She was still gaping like a fish as I slammed and locked the door behind her. I spun, leaning against the door, and looked up at Dean.

Maybe the old lady wasn’t the only one doing her best fish impression.

“Hey,” Dean’s smile warmed my soul.

“Dean,” I breathed. I couldn’t move. “You’re not dead.”

“Not this time,” he answered dryly.

I stared at him. His right eye was a little swollen. A cut marred his perfect cheekbone. He was standing a little off-balance, as though he’d injured joint in his left leg. The knuckles on his right hand had clearly been split open. None of the injuries were fresh; based on the bruises, I thought maybe three days old.

Dean took a small step forward, still outside my space. He licked his lips – which, miraculously, were undamaged, and spoke, “You look amazing.”

“Dean,” I flew into his arms, trembling. Tears I didn’t know I was holding back spilled over my cheeks. 

“It’s ok, baby. I’m here,” Dean dropped a soft kiss to the top of my head.

We stood there for a long time. Part of me wanted to unload all my fears and frustrations on him right then and there. But the part of me that just wanted to celebrate his return and take care of him won. I pulled back a little, looking up into those gorgeous eyes, “Do you want to get some pie?”

“Actually,” Dean swallowed. “I picked some up already. I thought, maybe…if you want…we could stay in?”

I stepped back, “Finally!”

Dean blinked, then threw his head back and laughed, “God, I missed you.”

***

I deposited the pies in the kitchen and led Dean into the bedroom.

“Take off your shirt,” I ordered.

“What, no foreplay?” he smirked. 

I raised my eyebrow, “Pants, too.”

“Yes, ma’am.”

“Definitely don’t call me that.”

Dean glanced up at me from where he sat on the bed, removing his boots. “Your Highness, then?”

“Mmm, better,” I watched as Dean revealed his body. More bruises and cuts littered his skin, overlaying older scars. None of the injuries, old or new, diminished his beauty. I moved forward, carefully straddling his lap.

Dean seemed content to let me control the pace. I ran my tongue over his lips, and he parted them, allowing me to deepen the kiss. My hands roamed his skin, but his touch remained light on my hips and waist. If not for the bulge pressing against my thigh and his soft sighs of pleasure, I might have thought him unaffected.

I’m not sure how long we kissed before I pulled away. I leaned back, running my hands over Dean’s strong shoulders. As much as he was enjoying himself, he remained tense. Whatever he’d done while he was gone was still on his mind. I could see it in the clench of his jaw and the tightened skin around his eyes.

Dean shifted uneasily, “What?”

“You’re so tense,” I cupped his face, my thumb tracing his kiss-swollen lower lip.

He shrugged, “I lead a stressful life. It’s no big deal.”

I ran my hands up the back of his neck, my fingertips tracing the lines of tension I found there. I pressed harder, rubbing the length of the tendons. My thumbs stroked the area behind his ears while my fingers massaged the base of his skull. Dean moaned, dropping his forehead to rest against my collarbone. My hands worked their way over his scalp, alternating between deep pressure, gentle scratches, and soothing touches.

“Feels so good,” Dean murmured against my skin.

My hands stroked down the muscles in that perfectly square jaw, gradually lifting his gaze to meet mine. I leaned forward, kissing his forehead, before dismounting. “Lie down, Dean. On your stomach.”

Dean scooted back on the bed, “Should I be nervous?”

I smiled, heading to my nightstand, “Nope.” I grabbed my supplies and turned back to Dean.

His green eyes tracked my movement, “Watcha got there?”

I held up the bottles, “Massage oils.” I climbed back onto the bed, dropping light kisses on Dean’s broad back. Fortunately, the wounds I’d seen on the front of his body stopped there. His back was unblemished.

“Mmm. I’ve never had a fancy massage.”

I laughed, “I don’t know how fancy it will be, but I can definitely help you relax.” I settled lightly onto Dean’s back before popping the cap on a bottle and warming some of the oil in my hands.

“Do all masseuses sit on their clients?”

“Hush, tough guy. You weigh like a hundred pounds more than me. Move your arms down,” I helped Dean rearrange before lowering my hands to Dean’s powerful shoulders.

I kneaded into his muscles, battling the stress locked in them. Dean groaned and moaned as each knot of tension was untangled. I continued down his back, twisting my fist into the knots under his shoulder blades. The heels of my hands forced the tension away from his spine. My palms smoothed tenderness from the small of his back. I hesitated only a moment before kneading Dean’s ass, drawing a surprised yelp that dissolved into a pleased whimper.

The massage was supposed to be for Dean. I wanted to make him feel good, I really did. It wasn’t about me. But I’d be lying if I said I wasn’t enjoying myself. Dean’s body was so strong, so powerful, so very _male_ – it did things to me. I had missed him so much, been so worried, waited so long to finally touch him – it was exhilarating, caressing his whole body, empowering to change his mood so profoundly.

Plus, the guy’s sexy as fuck.

By the time my hands stroked their way to his calves, Dean was a boneless mess on my bed, purring softly. I ran my fingers back up his body, relishing the feel of his strong form beneath me. I stretched over Dean, breath teasing his ear, “How do you feel?”

“Smohgoo,” Dean answered into the pillow.

“Sorry, baby, I didn’t quite catch that.”

Dean lifted his head, blinking languidly. He summoned the energy to smile, “So good.”

I smiled, kissing his temple, “I’m glad.” I shifted, starting to get off him.

Dean frowned. Before I realized what had happened, he flipped beneath me, hands on my hips holding me steady, “Where you goin’?”

“You looked like you were falling asleep. I was going to let you rest.”

“I don’t want to sleep,” Dean licked his lips. He shifted me back a little, and I felt his erection press against my ass. “I want to do something else.”

“Oh,” was all I managed before Dean’s mouth was back on mine. Gone were the passive kisses from earlier. These kisses were gentle, but intense. Dean explored my mouth thoroughly before dropping hot, wet kisses to my jaw. I felt his fingers in my hair, tugging lightly, exposing my neck to his wandering mouth. “Dean…”

“Mmm?”

“Oh!” Dean rolled his hips against mine, the friction sending a spike of pleasure through me. He flipped over again, and now I was on the mattress beneath him.

Dean’s mouth reached the collar of my shirt. He paused, pulling back. “Wait. Why aren’t you naked? You should definitely be naked.”

I laughed, “Sorry. I’ll get right on that.”

Dean grinned back, “Let me do it.” He leaned back on his heels, and I sat up, chasing his kiss. His fingers found the hem of my shirt, slipping just underneath it to tease skin. The feather-light touch caused me to gasp. Dean hooked the fabric between his thumb and forefingers of each hand. His hands flattened against me, gliding upwards from my waist, over my ribcage, up my shoulder blades, pulling the shirt up and over my head. My bra was only a moment behind.

I shivered, whether from the chill in the air or his touch I’m not sure. Dean kissed me again, exploring my exposed skin as I’d mapped his earlier. His hands slid lower, unbuttoning my slacks. Using the pressure of his kiss, Dean lowered me back to the bed. He tapped my hips, and I raised them. Dean stripped off my pants and panties, flinging them to the floor.

Dean paused, pulling back. His eyes roved over me, the heat of his gaze causing me to flush. He bit his lip and met my gaze. “You’re so beautiful,” his stretched over me, his lips just grazing mine. “Even more stunning than I imagined.”

I smiled, flattered by the sincerity of his compliment, “So you’ve imagined this?”

“So much. So, so much,” he nuzzled my neck, nibbling my collarbone.

“Mmm,” I tried to keep myself together for just a little longer. “Then why – God, that feels amazing! – why haven’t we done this before?”

He pulled back, brow furrowed, “Did you think I didn’t want you?”

I shrugged, “I didn’t know what to think.”

“Oh, baby,” Dean kissed me softly. “I wanted you. From the moment you called me clever, I wanted you. But…I’ve mostly been a one night stand guy. Like, my whole life. I’ve never really dated. Not like we’ve dated. And…”

“And?” I prompted.

Dean cupped my cheek, calloused fingers tracing my skin. “You’re special. Smart. Funny. I wanted to know you, like, as a person. You deserve more than just a good lay. I wanted to be sure,” he hesitated. “I wanted to be sure I could give that to you.”

I struggled to breathe. I took his face carefully in my hands, staring into his eyes, looking for a lie that wasn’t there. Finally, I pressed a chaste kiss to his perfect lips, “I missed you so much, Dean. Every day.”

“Really? Every day?”

His genuine surprise broke my heart. “Every damn day.”

Dean stared at me, I think looking for the same lie I’d been seeking. Then he kissed me, and the time for talking was definitely over. 

I sort of expected Dean to have some sort of definitive, mind-blowing move, something that no other man had ever considered. But I was wrong. It’s not that Dean did anything particularly special or different to my body. But what he did do, he did _very_ well. Dean was extremely thorough and in no rush.

Dean’s hands roamed everywhere. He varied the pressure and type – fingertips skating over my breasts, palms rubbing my ribs, fingers digging into my hips – noting every sound I made and adjusting his touch until every movement made me whimper. Then he caressed me with his mouth – wet kisses on my nipples, gentle nibbles on my collarbones, wide licks across my thighs – again experimenting until he was wringing the most pleasure possible from every inch of my skin.

It wasn’t just about me, though. Dean and I rolled on the bed, trading positions, allowing each other new angles to discover. I explored his body with my hands and mouth, too. He tasted like salt and oil and just…so _male_. His moans and growls of pleasure alerted me to what he loved – turns out Dean is a _huge_ fan of having his earlobe sucked and his waist nibbled – and I paid those places special attention.

My pleasure built to an excruciating arousal, “Dean…”

“Mmm?”

“Need you, please, need you.”

Dean looked up from the hickey he was creating on the crest of my left hip, “What do you need, baby? Tell me.”

“I need…” My mind was fuzzy with pleasure.

Dean perched over me, forearms caging me in. “Say it. Wanna hear you say it.”

I could feel his swollen cock rubbing against my entrance. It wasn’t enough. I thrust my hips. “Please…fuck me. Need it. Need you,” I whimpered.

Dean groaned. His tongue slid into my mouth at the exact moment he slipped a finger inside me. My cry was muffled by his kiss. His mouth dropped to my jaw, working upwards until his lips brushed my ear. I felt a second finger enter me as Dean spoke.

“Wanted this so long. Can’t wait to be inside you. You’re so tight, so wet. Perfect for me, baby. We’re both gonna feel so good,” He drew back, and I felt bereft while he rolled on the condom. A moment later he was back, body draped over me, face inches from mine. “I want to watch you cum,” he whispered.

Dean slid into me. Like everything else he’d done, there was no hurry. He took his time, watching my reaction as he filled me, inch by glorious inch. Once he was fully seated, he paused, eyes searching my face.

“Move, Dean, please, need you to fuck me,” I begged.

Dean smiled and rolled his hips.

I gasped, arching my back, releasing a litany of curses and pleas. Dean chuckled, “You’re so gorgeous.” He shifted, moving so he could set a rhythm. Usually, I’m all about being fucked hard and fast, but in keeping with the theme for the evening, Dean would not be rushed. He kept adjusting his hips, looking for the angle that would have me jolting off the bed with pleasure.

He found it.

Now Dean began fucking me in earnest, every stroke lifting me towards orgasm. I was overwhelmed with Dean – the scent of motor oil and aftershave, the taste of pie and coffee and salt, the low moans of pleasure in my ear, the cords of muscle flexing in my hands, the green of his eyes as he watched me writhe beneath him. It was incredible. I felt my orgasm building and I was begging for more, my fingers digging into his shoulders, reaching, reaching…

It hit, a volcano of an orgasm. Pleasure rolled over my senses like lava, hot and slow and engulfing everything else. It seemed endless. I felt Dean speed up, his thrusts harder, more primal, and I erupted again, fresh lava coating my already pleasure-laden mind.

Dean stiffened, then collapsed atop me. I mustered the energy to turn my head, dropping soft kisses on the skin I could reach, my hands idly stroking his back and arms. He laid there for a moment before rolling off me. I made a noise of protest when he stood, removing the condom.

“Be right back.” He reappeared a moment later with a warm washcloth, carefully cleaning us before tossing it aside. Dean climbed into bed, and I snuggled into his warm chest.

I could not ever remember feeling so content.

Sleep was coming for me, but I resisted. “Are you staying?” I murmured into his skin.

Dean stilled, “Do you want me to stay?”

“Yes!” I couldn’t keep the exasperation from my voice.

He relaxed and chuckled, the sound resonating through me. It was a nice sound. “Good. I like it here,” he dropped a kiss to my forehead. “Plus, there’s pie for breakfast.”

I smiled, kissed his chest, and slept.

**Author's Note:**

> I hope you'll forgive the slight change in flavor of this story. The fics featuring Sam and Castiel are definitely more one-night-stand in nature, which is what I tried to do in this story but...
> 
> I couldn't. I don't think the Dean from Season 11 wants that anymore. He has a home now, some stability, the chance to build relationships in a way he's never had the option to do before. So I let him. Nothing else felt natural. Also. If I got my hands on Dean, all I'd want to do is take care of him, which I don't think is something he'd allow a stranger to do.
> 
> (Yes, I know Dean is fictional. Don't care.)


End file.
